My short bio: Hey guys, I’m Jack. Some of you may recall my last AMA, shortly after I started my little project: Jack’s Flight Club (and that’s ‘flight’ not ‘fight’ …not to be confused with United Airlines’ new seating class).

You can check it out here if you like: Jack's Flight Club

We're nothing fancy… we basically send our members a note when flights to amazing places go really, reeeeaaaally cheap (like round-trip from UK to Hawaii at £289 cheap) and tell them where to book them before they are all gone.

In the last 5 months we’ve grown from a tiny membership newsletter of mostly my friends to over 75,000 members and, in the meantime, have saved travellers a ridiculous £500,000 on airfare - which I’m very proud of!

We’ve had stories of members getting to finally see their far-away family, get engaged, go on honeymoons, find new love, and visit places they never thought they could afford. It’s been a VERY hectic 5 months since the last one and I’ve decided to come back and host another AMA to answer any questions about our journey, cheap travel, and offer any advice I can for your next trip!

My Proof: That guy

So...ask me anything!

I’ll do my best to stick around after and answer them all - much more caffeinated and prepared this time around!

EDIT hey guys, the site is getting hug of death!! (not to mention my inbox) Try refreshing a few times and it should load if you are keen to check it out.

EDIT 4.5 hrs in Thanks for the gold strangers!! My back is killing me, and I'm going to grab a quick bite and stretch, but will be back in 10 min. I'll try to keep this going for a couple more hours at least. Sorry if I don't get to your questions until after that however - I don't think my keyboard has ever taken such a beating!!

EDIT Ok I'm back. BRING IT!!!

EDIT HUG OF DEATH ALERT! You guys seem to have brought me down.

EDIT OK guys I'm wrapping this one up now, thanks so much for all your questions and positive feedback. Been awesome chatting to all of you and catching up with existing JFC members too! I'll do my best go through and answer as many outstanding questions as possible over the next few days and get back to those that have emailed. Thanks again it's been loads of fun :)

Comments: 2055 • Responses: 87  • Date: 

rasel02620 karma

hey jack, I know you don’t often have time to help with individual bookings, but I just wanted to say that I’m still so, so thankful for your help bringing my father get back home after his flight got cancelled in US last year. You seriously saved us from an awful situation and asked for nothing in return. I know your list is much bigger now, but I just wanted people here to know the kind of chap you are.

To ask a question – now that your club is so much bigger, what does your typical day look like?

jack_sheldon1352 karma

Hey so glad I could be of help there and it all worked out in the end. Travel is stressful enough - add a cancelled flight and can get bad. Thanks for sharing that and for reaching out about it.

edit: sorry answered the wrong question here before!

My day is insane these days:

  • 4-5 hours of searching using mainly ITA Software matrix (Google's back-end flight search tool - you can check it out on my last AMA for more details) and sites like Momondo and others. I also use SkyScanner a lot for weekend trip deals (2-4 day short breaks around Europe)

  • Around 3 hours of answering emails (scattered through the day). It's gotten to take a lot more of my time, but was always a goal of mine to have my subscribers be able to communicate with me anytime.

  • Then working on the other little things like new functionality developments.

  • Then at the end I sometimes eat too :-)

IndeedHowlandReed202 karma

HI Jack, looking to go to Sri Lanka next year for the cricket. Anyways to bag upgraded flights cheap or is that a complete no go?

jack_sheldon193 karma

Hmmm not sure what you mean by upgraded cheap flights?

IndeedHowlandReed133 karma

Business class / First etc?

jack_sheldon386 karma

Ah - there's a chance, but honestly most of my deals tend to be economy as you'll see. I'll try to spot something if I can. Fingers crossed :-)

Toxic_Community41 karma

A general "rule" is that inter continental business class tickets are 4x the economy price.

jack_sheldon22 karma

That's basically the case - however sometimes they go down to 2.5x and as high as 8x or more. I usually only send out business class ones when there is some sort of error fare, but always recommend taking a look at he business class flights on the same flights the deals are for as they'll often also be discounted.

The correlation is not exact however, really.

ffxivfunk2437 karma

I get that you can save me money, but how can you save me from being beaten senseless by an airline?

jack_sheldon2420 karma

Disclaimer: not being beaten is not guaranteed with purchase of airline ticket.

MilkyStrudel2k15335 karma

But all the money you save on the plane ticket can be but into legal/medical expenses!

Jamaninja1046 karma

This guy's from the UK. Don't confuse him with terms like 'medical expenses'.

jack_sheldon667 karma

this guy knows!

MayorScotch578 karma

I hope this isn't an inappropriate question, but you mentioned that this is now your full time job.

How do you make money from a newsletter?

jack_sheldon1283 karma

I have a premium option for those who want to get some extra perks like more weekend trip emails and get ALL the deals. There's also a free version which gets a deal or two a week :-) The premium one helps me pay the costs to keep sending emails to so many people, as I don't like ads and prefer not to work with affiliates like other sites

It still doesn't pay what my job used to and I work twice as much, but it's 100% my fav type of work!

MayorScotch286 karma

So you can also pay rent and all your bills from this?

Is there any advertising?

Thanks for answering :)

jack_sheldon732 karma

No advertising - just word of mouth really so far. People tend to share a lot when they score a deal, which is nice!!

I can pay my rent/bills if I live frugally in cheap(er) countries, so that's what I'm doing these days until hopefully we grow a bit. Can't complain as it beats a 9-5 and travelling is my passion anyway!

naeads133 karma

You staying in Chiang Mai (Thailand) by any chance? That's how Uber did it.

jack_sheldon159 karma

No, not Chiang Mai, but I've been and can see why they did it there!

I spent last month in Mexico and am currently staying with a friend in Ukraine actually. Hoping to move onto somewhere with a beach soon!

wishod63 karma

Hello from Ukraine! Life is quite cheap here nowadays, as you may've noticed.

jack_sheldon62 karma

Indeed - not a bad place to stick around if you are trying to save and come from abroad! Thanks mate!

MayorScotch12 karma

I meant do people pay you to advertise via your newsletter. :)

jack_sheldon113 karma

I've had some offers, but I don't really want to put my name behind something like that unless it's 100% something I believe in. I don't do ads at the moment at all.

chandler25371 karma

Describe in one word what you think of United Airlines?

jack_sheldon1044 karma


Edit: But seriously, for whatever reason, overbooking seems to be a lot more commonplace in US than it is elsewhere and it a bigger issue, even though it is technically legal in most regions. Overall I think US-based airlines are the worst globally, both in service and the way they treat customers. What United (and the police) did there was inexcusable. You’d think the guy had a weapon the way they threw him out of the chair. Completely fucked up.

That email from the CEO was just ridiculous really!

SoundBearier246 karma

The flight wasn't overbooked. It's way, WAY worse than that. Overbooking is a gamble... this is something else entirely.

jack_sheldon26 karma

Agreed. No excuse here.

chillourtbruh2 karma

Do you think the world would care if the passenger was Muslim? Do you think the narrative in all the headlines would be the same? Do you think reddit would be so outraged?

jack_sheldon11 karma

I probably shouldn't answer politically heavy questions using this account buuuuttt I'll bite. I'm not sure a news story can possibly get any bigger, I just think the narrative would be different if he were Muslim. It's a fucked up situation no matter what he is. Shame on United here

10CPFC353 karma

So given the hysteria around United Airlines at the moment and your vast knowledge of the air transport system, do you think a boy will be born who can swim faster than a shark?

jack_sheldon420 karma


Also aquaman already exists and I can only image how many mermaids he's knocked up to date.

lifetotheminimum300 karma

Hi Jack,

If you're ever hiring, keep us (me, strictly me and only me) in mind.

My questions, where do you see this going? Are there any major milestones you would like to reach?

jack_sheldon221 karma

hehe will do. Send me an email and I'll put a star next to it if it ever comes to that! Fingers crossed we get there!

ShavingRegret182 karma

Hi Jack. I got your Paris - Tokyo - London deal as soon as it came out so am really looking forward to that!

Have you got tips for Hong Kong flights? It's rare I see them coming in too cheaply from London

jack_sheldon148 karma

HK has come up a few times before, usually on an awesome non-stop from London with Cathay (#1 airline last year I think), but we're overdue for one now I'd say. Have an amazing time on your Paris/Tokyo trip, that was a popular one, you never know you might be sitting next to another JFC member :)

ShavingRegret71 karma

JFC members will be an easy group to identify on that flight cos we'll be laughing the whole way over!

jack_sheldon37 karma

Seriously if you ever run into another one, I HAVE TO know about it!

The_Fappering10 karma

How much was it?

ShavingRegret21 karma

Around £310 return

IAmNotStelio11 karma

Holy fuck!

jack_sheldon15 karma

It's as low as £248 right now if you book it for winter 2018

grebfar107 karma

How much does it cost you to advertise on /r/iama?

Crackmacs91 karma

Hi Jacking your reply with Hi Jacks


Edit: every single one of these accounts also commented within the last 3 hours.

Edit 2: 60 instances of "Hi Jack" in the thread right now.

Edit 3: It's absolutely possible that people just don't use for a month then randomly show up and make a post, but come on, this is way too coincidental.

Edit 4: Jack said it's all good.

jack_sheldon44 karma

I replied to this above guys: just to be clear here - I let some of my subscribers who use reddit know that I'm doing an AMA in case they wanted to ask for advice or help with travel plans.

trevor2574 karma

Which of your deals has been booked by the most people?

jack_sheldon159 karma

Good question… it would have to be Aeroflot’s ridiculous mispriced open-jaw fare to Tokyo at around £248 return. I’m fairly certain at least 250 people booked that one (that I know of!) from my alerts. It’s come around a couple of times in the past as Aeroflot for some reason seem to either be fine with that pricing or are so oblivious that they are still not aware. One thing is for sure - they are not making money on it!

Edit: I should clarify: ‘Open Jaw’ basically means that it departs from one city and return to another. In this case it departs Paris (CDG) and returns to London (LHR).

Edit 2: Woaaaaaaa just looked and it’s still around from my last email (though the XMAS&NYE dates are gone now)! If anyone is interested, go here to find the cheapest dates, but don’t book there as they’ll charge £20 in fees on esky. Head over to and book with one of their OTAs or directly by putting the same fare into google flights instead and booking with Aeroflot. Their website isn’t great, but you’ll get a ticket! PM me if you need help and I’ll try to get to it after this AMA.

SoundBearier162 karma

But then you have to fly Aeroflot.

Aeroflot: when you stare into the abyss, remember who flew you there.

jack_sheldon87 karma

Aeroflot has a bad rep from the past, but they fly the same airplanes as everyone else now (western ones haha) and the service is quite good. I wouldn't hesitate really

CavanG2654 karma

I booked it, can't wait for my 2 weeks travelling through Japan. Cheers !

jack_sheldon46 karma

nice one! just now?!

SoundBearier18 karma

I've actually never flown with them, but my father has. He describes it as the most terrifying experience in his life. Granted this was back in the 90s when they were widely known for being genuinely scary.

jack_sheldon31 karma

Aeroflot had their own planes in the 90s... I would be terrified as well!!

FizzyGizmo22 karma

I booked your last offer to Tokyo via Paris on the outbound and Amsterdam on the return. I've wanted to do to Tokyo all my life and had always put it off because of the cost but to get a return for basically £300 meant it was finally achievable. Thank you

jack_sheldon26 karma

Brilliant!!! Soooo many people booked this one - there are probably airplanes filled with JFC members lol

SharpyShamrock60 karma

Hey Jack,

Some of your deals are a little bit creative, in the routes and specific flights you recommend. Do you have any personal rules that have stopped you sharing particular deals?

For example, you might have spotted a route to NYC for £275 but its 32 hours and has 4 changeovers so you don't bother. Forgive me if this is a stupid question I'm not sure how you actually set up the deals.

Great service I hope to be able to book on one of your recommendations later in the year

jack_sheldon74 karma

pretty much - I aim to balance great prices with convenience. I personally would avoid taking a flight that's £100 cheaper but has 2 long layovers or something crazy like that. Or if layovers are overnight in some city, there really is no benefit if you have to grab a hotel and a bus from the airport just to grab the savings.

Hmmmm I have a bunch more - will have to come back with those

StopMakingScents21 karma

What about people like me who love layover that are around ~24 hours?? I fly a lot and always try to get an extended layover in a new city on the route. Any tips?

thelardboy49 karma

24hr layover in Amsterdam or Vegas? Hell yeah! 24hr layover in Doha, Qatar? I'll pass.

jack_sheldon13 karma

Yeah really depends!

jack_sheldon18 karma

I do a lot of deals that have a 'nice' layover. For example arrive mid-day in Amsterdam and spend 24-36 hours there before flying off to Bangkok or whatnot the following evening. Those are fantastic!

The ones I try to avoid are 12 hour layovers where you arrive in the evening and basically depart early morning. Not much you can do then apart from sleep at the airport.

Rikolas55 karma

Hi Jack, been subscribed since your first Reddit AMA and love what you're doing!

Question: I've wanted for 16 years to go to Japan and can finally afford to do it now next year - Do you ever see error fares so far in advance? All the ones you email seem to be within the next 9 months or so? I'm hoping to go in either March or September 2018!


jack_sheldon66 karma

Amazing, you'll love Japan, worth the wait! Error fares appear randomly so it's hard to say when they'll come up but I've seen error fares that you can book ahead for a max of about 8-10 months.

Rikolas19 karma

Thanks for replying! Now I don't know whether to book it asap or wait a few months and see if some error fares come up in my time periods? decisions decisions!

jack_sheldon28 karma

Did you see the comment about the open-jaw flights to Tokyo with Aeroflot? Those are now available in early March as well! I would wait another week or two and try to grab them for mid-March 2018

SmoothThatRuckus39 karma

How is ths any different to other cheap flights sites like Airfare Watchdog or Scotts Cheap Flights?

jack_sheldon29 karma

Those are 2 slighly different categories there but Scott Flights are a great resource too - they started in the states and I started JFC here in the UK. We are similar in that we both find and send out lots of really cheap long-haul deals, but i try to cater JFC towards travellers like myself, who may take a trip or two per year to somewhere like Asia or S. America, but will also want to do a few weekend trips to Europe along the way.

Other sites make a big deal out of £25 RyanAir fares to wherever in Europe, but most of my subscribers can’t take a off 3 days mid-week to save a few £ on a cheap fare, so when it comes to quick getaways, I try to focus on balancing convenience and price and send out Friday - Sunday trips and focus on bank holidays. I don’t think there are many others doing that as it doesn’t give the same ‘wow’ factor.

Airfare Watchdog is another great resource for Americans as well, but I find websites in that category tend to push what I call ‘hotel spam’ and ‘car rentals’ as that is where they make their money. I try to aim for providing only useful info and cheap flights - no referral fees or commissions to worry about, so the incentives line up with what my subscribers are after

john21729 karma

Yo Jack - I want to take my little brother somewhere in Southeast Asia (he’s not been yet), but he’s afraid of flying and hasn’t travelled much before, so I want to minimise the number of flights as much as possible and was hoping to go direct. Thinking late August or early Sept. Still not sure where, but maybe Thailand or Vietnam. Got anything for us?

Edit: Oh and we’re in London!

jack_sheldon49 karma

Hey man - awesome of you to take your little brother on a trip like that. I personally like Vietnam, but would probably choose Thailand for a first trip to SE Asia for your bro. These aren’t the best fares I’ve seen by a while, and they could still come down another £50 at some point, but EVA Air currently have some attractive non-stop fares which should make travel easier. It’s a top 5 airline with a direct flight to Bangkok - doesn’t get too much better than that for a first trip! :-)

Here’s a link

Whapwhaaap1 karma

I'm also hoping for cheap flights to SE Asia In early Sepetember!

jack_sheldon2 karma

should be lots of options to SE Asia then - it's off-peak season, so should be some price drops in the future I think. I'll keep my eyes peeled!

lurkingforthelols20 karma

Thanks for taking the time to do this. I am yet to have taken advantage of your deals but they give me hope I can afford to go to some places I thought I wouldn't be able to.

How often do airlines honour the error fares you sometimes send out?

jack_sheldon25 karma

It's usually 50/50 I'd say in terms of them honouring, always wait at least a week before booking your accommodation.

We had an amazing error fare from Edinburgh to the OZ not long ago at something around £290, and it was pulled almost 2 weeks later. I've never seen anything like it, so I always warn to hold off as long as possible just in case.

terriblebugger18 karma

What's the tastiest error fare you ever managed to snag for yourself before Flight Club?

jack_sheldon32 karma

I think I mentioned this one in the last one. For me £112 to Bali ages ago. Was one of the happiest days of my young life back then! :-)

ajame510 karma

We've just booked our Honeymoon to Bali and was hoping there'd be something like this come up recently. Just wanted to say thanks anyway as we managed to get all our flights for the entire trip (Kuala Lumpur, Singapore, Bali) much cheaper from playing around with the Momondo/Google combination that you seem to use. You saved us a fair bit, even without an actual deal.

I nearly pulled the trigger on that £97 New York fare last week but sadly couldn't go!

jack_sheldon9 karma

Sawweeeet! Well done using those tool... I find the best services I use also educate a bit, so I was really going for that when I started - even better that you were able to find your own deals really. I spent my honeymoon in Bali as well and it was amazing - I'm sure you'll love it!

terriblebugger6 karma

Uff so jealous. How do these things still happen with so much of it automated?

jack_sheldon34 karma

Massive massive complex pricing databases which are then forwarded to bookings agents who price based off of those and other agents which match fares of those agents and yada yada yada. One mistake by anyone, anywhere and it can get multiplied onto a dozen websites sometimes.

Big data = big mistakes :-)

CustomBlendNo114 karma

Thanks for doing the AMA, Jack!

A few questions:

  1. I assume this is now your full time job? What other jobs have you had in the last 5 years?

  2. Given you can probably work from anywhere in the world, how much of your average year do you spend abroad?

  3. Do you plan all your own travels around cheap tickets, or do you occasionally splash out and pay full-fare for convenience?

jack_sheldon17 karma

Hey thanks for coming by to visit! :-)

1) It is now - I've never worked this hard and never absolutely loved it. It's mental!

2) Well I only went full time a few months ago, but since then it's been basically 100%

3) I always fly as cheap as I possibly can, but not always with the deals I find - I have in mind where I think I want to go next :-)

iamdiddy13 karma

Hi Jack! I actually came across you via Reddit from someone who recommended you. Just one question really - what is your ambition for the company? Is it scaleable?

jack_sheldon26 karma

I hope so!

I just plan to grow and create a community of savvy travellers and JFC members. I DONT want to be like everyone else and start pushing hotel spam or car rentals or start taking commissions from booking sites that don't always offer the best deal on a particular flight.

We also plan to grow a bit - starting with Europe this year!

Melchair12 karma

Is there an optimum amount of time before the actual flight that you find your deals? I'm looking at subscribing in 3 or 6 month chunks but don't know how far in advance of my travels to begin the subscription. Or would you recommend 12 month subscriptions to take advantage of everything you find?

jack_sheldon20 karma

It varies vastly by airline and season. Some of these new-age budget long-haul airlines like Thomson tend to have tonnes of last minute deals a few weeks prior, while major airlines usually have their best offers 8-12 weeks in advance and some scattered price drops as far as 11 months in advance.

Had a lot of members book that Hawaii trip for Jan 2018 recently!

squishynurse9 karma

What's your favorite kind of cheese?

jack_sheldon22 karma

Cheese strings (String Cheese in American). What does that say about me? lol

lurkingforthelols8 karma

Is it possible to rock up at the airport and get yourself a last minute deal if you are flexible on location or is the price even higher?

jack_sheldon11 karma

nah - very rarely will you score something like that. Usually you'll end up paying 2x the standard fare :-/

It does happen with some budget airlines, but even then very unlikely

Merboo7 karma

Hi Jack!

I've been signed up for about four months so far, and although I haven't booked anything yet, I'm loving it all so far! I'm sure I'll book something soon.

How long does this all take you each day? Do the stories make it all worth it?

jack_sheldon11 karma

Flight searching takes 4/5 hours a day and answering emails the same again. Yes I love the stories that come back from people telling me they are off on holiday and I get some cool ones like people that are off to see family they haven't seen in years or for honeymoon trips etc. Glad to hear you're loving it so far.

Phlebas995 karma

Is there ever going to be a way to know what's coming up? Probably impossible.

I've been signed up since the start and are part of the paid group, but I've yet to actually book anything because I tend to want to over plan holidays and so am struggling with the idea of booking as a deal appears, and not knowing if or when that will be.

jack_sheldon8 karma

It's impossible to know what will come up next, that's part of the excitement I guess! There are trends to it - for example booking flights from Europe to Australia and NZ is often cheapest in Dec-Jan and then again during summer. But no way to tell exactly when prices to a certain destination will fall. You just have to wait and see....and scour (which is what I do!)

A lot of deals let you book months ahead though so that might help you have time to get organised when you see the flight you want.

sappy165 karma

Hi Jack,

I love getting your emails. Haven't booked anything yet but it's only a matter of time :)

Do you have any tips on how far in advance to start looking for flights? I recently booked a trip to Lisbon (from London), but waited a short while hoping prices would go down - I had price alerts set up with Google Flights. They ended up going up instead so I paid more than I would have if I had booked earlier :(

jack_sheldon8 karma

Usually 8-12 weeks before is a sweet spot, but it varies a lot by airline, route, and season. Leave it too late and airlines try to capitalise on hiking the fares for business travellers. But this varies by season - peak season you want to book as far ahead as possible, off-season - some airlines have last min deals, especially budget long-haul liners. Yes keep an eye out and let me know when you book pls :)

kshatriiya5 karma

Hi, are you looking for volunteers?

jack_sheldon5 karma

Maaaaybe, send me a pm :)

fluffyballofdeath4 karma

Hey Jack,

Thanks for all the great offers to date! I missed out the on cheap option to join the members list last month. Would the original link sent out still work and would you honour it if I was to join the premium later this month? :)

jack_sheldon5 karma

Sorry - I couldn't keep that offer active as it wouldn't be fair to all those who signed up back then. You know? Give me a shout on PM however so I can understand what you mean

dcarro144 karma

Hi wanted to say thanks for all the amazing deals been on your newsletter since the first ama. My girlfriend and I are going to SE Asia in the summer (July 17th for 3-4 weeks). Thinking Thailand and Cambodia. Got anything for us? Or for any countries nearby you would recommend?

jack_sheldon4 karma

Pleasure, thanks for joining. I'd include Chiang Mai in north Thailand and then look into looping into Laos from there and maybe Vietnam if you have 4 weeks!

ronak_954 karma

Hi Jack! Thanks for the service, managed to send my parents to Dubai a few months ago thanks to your help!

Since your sudden growth to 75 000 members have you had airlines approach you about the service you provide? Whats their take on it?

jack_sheldon4 karma

Perfect, hope your parents had an amazing time. Not been approached by the airlines as I don't think we're big enough to get on their radar yet!

chillourtbruh4 karma

Is this something that's only available in the EU? Can we subscribe globally as well?

jack_sheldon5 karma

Right now we're live just in the UK but have plans to expand at a later date to Europe/US and Australia. If you're in one of these regions you can get on the notification list from the link at the top.

Chc06jc3 karma

Hi Jack, I just wanted to say thank you. Thanks to your email alerts my fiancé and I were able to book cheap flights to San Francisco for less than £600 (return for two). I am so looking forward to it!

Reading your alerts makes me wish I could just hop on a random flight and see the world!

My question: do you do a tailored premium service where someone can specify a country (or countries) of interest and get notifications for when flights to/from that country are cheap? Could your algorithm do that?

jack_sheldon4 karma

My pleasure, you'll love San Fran, and yes the emails tend to have that effect haha. I don't do a bespoke service I'm afraid as would just take too much time to look after people individually, best to have in mind where you might want to go next and keep an eye out for the alerts.

heyyanny3 karma

Where was your most disappointing holiday?

jack_sheldon7 karma

Once went to Cancun and had food poisoning the whole week when I was supposed to be partying with my friends :(

grwtsn3 karma

Hey Jack! Thanks for doing what you do - I've got four days in Mallorca coming up thanks to you, so cheers!

My dream holiday would be to the Azores (ideally flying in and out of Ponta Delgada), but they're a nightmare to get to - any tips?

jack_sheldon4 karma


TAP Portugal just revamped their pricing completely and offered a new fare class, which has created lots of deals for Europeans. Take a look and see if they have anything. I'll try to remember to look at it after this AMA as well!

TheOldKanye3 karma


jack_sheldon12 karma

Hmmm some of these online travel agents (OTAs) can be a bit scummy and try to call you minutes after booking and tell you the flight is no longer available and you'll have to pay more for it.

When that happens, stick your ground and refuse to pay more. They'll usually give in or something refund your fare - in which case go on and book with another website.

Other than that, error fares will sometimes get refunded within a day or two of booking, but I always warn of that!!

crazyc13 karma

Hi Jack,

I just signed up to your Premium service yesterday, in fact, after reading your last AMA.

I know your deals are normally 3-12months in advance but I was wondering if you find many cheap deals in the 0-3months time zone?

Im last minute summer holiday hunting!

jack_sheldon3 karma

yeah definitely. Thomson often offer tonnes of cheap last minute deals. There are some non-stops to Orlando from UK right now as well as Dominica Republic. They charge a bunch for extra bags, but if you pack light, it's really a steal!

UltimateKitty3 karma

Hey Jack, what's the craic? Just wanted to say thanks for what you do, you helped my friend get back to South Africa for half the price on BA! Have you ever got an amazing story from a person who used your service?

jack_sheldon6 karma

Thanks for being part of it, glad you got your friend the SA flight. We had a lady that got to go to see her family in Colombia for the first time in ten years which was amazing. Also got a guy at the moment who's taking his Mrs on a surprise trip to Bali so he can propose to her, fingers crossed.

RyanLloyd13 karma

Hey Jack, just got the e-mail that you were here!
My favorite place in the world is Boston and flew from LHR last time we went. It seems the last year has seen some big discounts in flying from UK to East Coast US. Do you see this becoming a trend and the price of trans-Atlantic getting lower and lower?

jack_sheldon4 karma

Hey Ryan, there's new routes and airlines popping up for UK to East Coast (Norwegian Air for example) and it looks like some of the low cost carriers are trying to serve this market so yes that can only mean good things in the future for these prices.

sparkchaser3 karma

First, I have signed up for your email and several of my coworkers have as well.

My question: if I find an itinerary on ITA AMtrix with a the carrier and a booking class I want, how can I book it? I am aware of the book with matrix site but it doesn't always work. Thanks!

jack_sheldon3 karma

Thanks for spreading the word, maybe we can get our first work team flight booking and get you guys to have a meeting somewhere exotic, I'll have a word with the boss ;) When you find the details you then have to search the same flight on Google flights and that will serve up booking links with the airlines.

beelalol3 karma

Do you have any websites you commonly use to find cheap deals? I've always stuck to skyscanner but was wondering if there were other websites that could be of use too?

jack_sheldon8 karma

I spend a lot of time in Google's backend matrix, it’s slightly more complex but gives you better results: tip - also try changing the sales city at the bottom and you may be surprised at the difference in price sometimes.

Once you find a cheap fare on google you should check other sites to see if you’ve really got the best deal, I use for example which picks up fares from the cheapest agents.

If you’re flexible with the amount of stop-overs then also checkout They search a lot more options for each route than Google and Skyscanner for example.

c_diddy2 karma

Hi Jack

Do you ever take advantage of your own deals and if so where is the best place you have been so far in your travels?

(Current member and loving your work!)

jack_sheldon4 karma

Not as much as I'd like to! This little project has kept me crazy busy, but these days I try to travel somewhere and hole up in a hostel for a month or two to work and soometimes enhoy going outside!

it_am_silly2 karma

Is there anywhere you really want to find a deal for, but haven't managed to yet?

jack_sheldon7 karma

Bora Bora is on my hit list but still not managed that one yet!

k1_yo_brp2 karma

Hey! Thanks for what you do - I'm a subscriber! Do you think there is any chance of discounted fares in August? I need to go to Boston (from the UK) and all of the cheap fares I've seen to the East Coast in the past few weeks have been outside August. Ugh!

jack_sheldon3 karma

July/August are the worst! Price drops do happen, but not nearly often enough. I would say set some trackers for the second half of Aug in google flights and see if the prices change in the coming week. I'll keep an eye on Boston for you as well - fingers crossed!

54442 karma

I managed to snag a £16 one way flight at 6am from Inverness to London on Saturday 22nd April. The next flight out was at 3pm and would've cost £70. Did I accidentally come across a fare error and snagged it?

I am also a paid subscriber to the Flight Club, always on the look out for a fare that matches our travel plans. Few of those Japan ones were very tempting as we really really want to go back!

jack_sheldon3 karma

which airline??

crappy_unicorn2 karma

Yo yo Jack! What's the worst airline you've ever flown with and why?

jack_sheldon3 karma

The one ranked the worst by Skytrax is Koryo Air a North Korean airline. For me the worst I've been on is Ryanair (sorry if it's an obvious answer!)

murfs2 karma

Hi Jack, Most of your flight deals are based on being extremely flexible on dates/times but do you have any tips for the cheapest ways and means of getting flights at specific times/dates given you know in advance? Is there a particular time that will be cheapest, or it it best to just set up a Google flight tracker and wait?

jack_sheldon2 karma

I'd say check out hopper (it's an app), but also setting google flight alerts is a good way to go. They send you updates when flight prices fluctuate

orodonyx2 karma

Welcome back Jack! I'm wondering, does your newsletter deliver worldwide? Would be nice to have an opportunity to travel, and this would definitely help. Great service you provide!

jack_sheldon5 karma

It will soon I hope! Planning some growth in the near future - I've been trying to perfect it in the UK first :-)

lemonsparty2 karma

Hi Jack, was there any pressure from airlines when they had error fares?

Also, what's next, about Jack's flying club? Will you be sending flights from outside oc UK?

jack_sheldon5 karma

Not had any pressure/issues with the airlines yet, and yes plans to expand into Europe, US and maybe Australia in the future but right now all the focus is in the UK as that keeps me real busy!

Jazzauk1 karma

Hey Jack just wanna say thanks. Me and my girlfriend just booked our honeymoon 2 for 1 trip to dominican republic via Barcelona saving us a fortune. This is a dream trip for us and we now have more cash for our wedding. I will defiantly be using your flights in the future!

Also have you had any backlash or complaints from airlines. For costing them money / letting people know about error fairs?

jack_sheldon2 karma

Yessss!! Nice one - I was really surprised by how many people booked that one given that it only went to premium and wasn't even out of the UK. Well done :-)

No complaints from airline - we're still small fry to them!

L11VYK1 karma

Hey Jack! I've never been so excited to receive an email as I do when I see your name pop up 😊 I just subscribed a month ago to your Premium service and I love it. I'm still kicking myself that I didn't snag the £280 flight to Vegas. I saw your email last night about flights to LAX, but September is only available from Dublin (and a subsequent overnight stop before the early morning flight) so it's out of the running for me. Finally, my question is: is there a day or time that tends to be cheaper to book Flights? I heard that prices go up later in the week. P.S you are 👌😉😍

jack_sheldon1 karma

haha that's cool, happy to brighten up your inbox. It used to be that certain days/times affected things but not anymore, it's really just a case of when they come up which could be any day.

shahidzain671 karma

Hey Jack, just signed up to your website now as I love to travel. I was wondering, if I flight comes up once is it likely to come up again in the future or are these more like 1 time deals? I'm hoping to go to Costa Rica or Japan from the UK but they are both out of my budget atm.


jack_sheldon2 karma

Hey thanks for signing up :) Yes goooood news the just looked and the Tokyo deal it’s actually still around from my last email (though the XMAS&NYE dates are gone now)! Go here to find the cheapest dates, but don’t book there as they’ll charge £20 in fees on esky. Head over to and book with one of their OTAs or directly by putting the same fare into google flights instead and booking with Aeroflot. Their website isn’t great, but you’ll get a ticket!

Yes also had Costa Rica come up a couple months back so it does appear :)

Whapwhaaap1 karma

Hi Jack! I signed up a couple of weeks ago to premium and I love it! I actually emailed you two days ago with a request and was surprised how quickly you replied (and that you did at all!) so thank you!

I wanted to ask how do you choose destinations for your deals? Do you wake up one day and just randomly decide to look for flights to the US, or is there some sort of system that you use to figure out where will have cheap flights that day??

Also do you employ others, or are you working alone?

jack_sheldon3 karma

Try to get back to everyones emails - it's what takes up a solid 30% of my day hehe.

I do have a system but it's more based on what becomes available and less where I'm thinking of. I can't really control the airlines unfortunately so I'm just here to capitalise on their price drops and help other do the same!

Recently brought on a partner to help me out but not big enough yet to have any employees (or even pay ourselves yet) Hopefully one day for both! :)

L11VYK2 karma

He's replied to me a few times too, amazing service!

jack_sheldon2 karma

why thank you ;-)

Bluey220 karma

Congratulations on all of those subscriptions... I became a member a few months ago and although I've not yet booked a flight yet I'm so tempted every time I see your emails. Anyway onto my question.... Have you had any problems or issues with airlines?

jack_sheldon0 karma

Thanks, appreciate it. No issues yet luckily, I don't think we're big enough to get on their radar yet.

winterjoey0 karma

Hey Jack! I'm always wary of error fares despite how cheap they are. How often do you see error fares being rejected by the airline after they're sold?

jack_sheldon0 karma

It's about 50/50, and with the absolute best ones, the chances of being honoured these days go down to 25%. We had a recent £97 one to NYC, but sadly it was refunded.

Never any harm in trying however! I've seen ones like that get honoured in the past!

Powerballwinner21mil0 karma

When will you have US and Canada and why don't you yet?

Do you work with any travel agencies?

jack_sheldon2 karma

It's coming - hoping for later this year but really depends as I don't want to start until I know the quality is there!

I don't work with any travel agencies - I think that's the downside of other sites as they get commission and therefore their incentives are then misaligned with the person they help :-/ Maybe I'm overly-negative about them though